Thrift Shop Date
This is a activity that can add fun and excitement to any date. It works best of you plan the date to take place somewhere that there are a lot of people around.
Before going to the designated spot, stop by the Good Will, Salvation Army or local thrift shop together. Once there, specify a small amount ($1.00 - $5.00) to purchase clothing or accessories for the other person to wear for the rest of the evening. Set a time limit of 10 or 15 minutes to search and you should both head off in different directions to look for something for your date to wear.
The goal is to find items the other has to wear for the rest of the day/evening within the price and time limit specified. The entertainment is seeing the reaction from all the people who see your new accessories or clothing as you wander the crowded area.
This date is better to do with someone that you are somewhat familiar with since you don't want to embarrass a first date by picking something they have no desire to wear. If you are familiar with your date, however, you can have a lot of fun with this for only a few dollars.